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The school was founded in 1912 as Montgomery Industrial School. The school President was Henry P. Carpenter. It underwent a major expansion in 1921, when two new buildings were built for a cost of almost $40,000, including a concrete block dormitory for 200 boys and a new dining hall. The expansion was funded by donations, including $11,000 from R. Jay Arnold of Groveland, Florida. This expansion brought the organization to a total of 8 buildings on 200 acres and $150,000 worth of equipment. An observation tower above the new dormitory provided a view of Lake Apopka, Winter Garden, and Groveland. The dining facilities served 400 children.[3] In the 1920s, sports teams were established. The teams used were nicknamed The Crackers. In 1930, a girls dormitory was constructed with funds raised by the D.A.R.[4]

Montverde's athletic programs compete on a national level, rather than as a member of the Florida State High School Athletic Association. Sports offered include baseball, basketball, cross country, equestrian, golf, lacrosse, powerlifting, soccer, softball, swimming, tennis, track and field, and volleyball.

In 2017 USA Today named Montverde Academy the best basketball program of the decade.[5]

In May 2017, Essence and Fox 35 Orlando published a story about Montverde Academy harassing a 16-year-old African-American student who was told that her natural hair was against dress code policy.[6][7] The school's headmaster, Kasey Kesselring, promised that the "dread lock" line would be removed from the hair policy in the student handbook.[7]

In 2007, Montverde Academy was sued for not returning $36,000 for tuition and boarding fees for the 2007–08 school year after expelling a Russian student who was allegedly spotted with alcohol, without giving the student an opportunity to contest the truth of the allegations.[8]